#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:54:34 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261586 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241468.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7241468
loop_
_publ_author_name
'Tan, Sang Loon'
'Lee, See Mun'
'Lo, Kong Mun'
'Otero-de-la-Roza, A.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Experimental and computational evidence for a stabilising
 C--Cl(lone-pair)⋯π(chelate-ring) interaction
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              119
_journal_page_last               130
_journal_paper_doi               10.1039/D0CE01478H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C19 H22 Cl3 N S2 Sn'
_chemical_formula_sum            'C19 H22 Cl3 N S2 Sn'
_chemical_formula_weight         553.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-10-08 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.0345(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.15307(7)
_cell_length_b                   16.49930(13)
_cell_length_c                   13.41809(10)
_cell_measurement_reflns_used    18348
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      76.3740
_cell_measurement_theta_min      4.2220
_cell_volume                     2230.86(3)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27048
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.084
_diffrn_reflns_theta_max         67.084
_diffrn_reflns_theta_min         4.266
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    14.193
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   CrysAlisPro
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.383
_refine_diff_density_min         -1.523
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0374P)²+1.2010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3859
_reflns_number_total             3980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01478h2.cif
_cod_data_source_block           shelx_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7241465--7241470.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7241468
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.170
_shelx_estimated_absorpt_t_max   0.459
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn Sn 0.75942(2) 0.32133(2) 0.36526(2) 0.01612(7) Uani 1 1 d . . . . .
Cl1 Cl 0.88297(5) 0.36603(3) 0.52460(4) 0.02500(12) Uani 1 1 d . . . . .
Cl2 Cl 0.97095(7) 0.60658(4) 0.07295(4) 0.03399(15) Uani 1 1 d . . . . .
Cl3 Cl 1.08374(8) -0.02457(4) 0.33062(6) 0.04416(17) Uani 1 1 d . . . . .
S1 S 0.55414(5) 0.34594(4) 0.44058(4) 0.02288(13) Uani 1 1 d . . . . .
S2 S 0.55281(5) 0.27643(3) 0.23874(4) 0.01956(12) Uani 1 1 d . . . . .
N1 N 0.33065(19) 0.30720(12) 0.32054(15) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.4616(2) 0.30948(13) 0.33067(17) 0.0185(4) Uani 1 1 d . . . . .
C2 C 0.2474(3) 0.32950(17) 0.4010(2) 0.0300(6) Uani 1 1 d . . . . .
H2 H 0.153710 0.318759 0.371648 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2719(3) 0.2749(2) 0.49299(19) 0.0388(7) Uani 1 1 d . . . . .
H3A H 0.271114 0.218051 0.471568 0.058 Uiso 1 1 calc R U . . .
H3B H 0.202066 0.283603 0.536153 0.058 Uiso 1 1 calc R U . . .
H3C H 0.358428 0.287776 0.530397 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2530(3) 0.41939(19) 0.4258(2) 0.0446(7) Uani 1 1 d . . . . .
H4A H 0.340660 0.432852 0.460807 0.067 Uiso 1 1 calc R U . . .
H4B H 0.184729 0.432389 0.468979 0.067 Uiso 1 1 calc R U . . .
H4C H 0.237093 0.450902 0.363558 0.067 Uiso 1 1 calc R U . . .
C5 C 0.2566(2) 0.27336(16) 0.22613(17) 0.0249(5) Uani 1 1 d . . . . .
H5 H 0.321362 0.267894 0.176034 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1462(3) 0.32887(19) 0.1808(2) 0.0420(7) Uani 1 1 d . . . . .
H6A H 0.075676 0.330328 0.224450 0.063 Uiso 1 1 calc R U . . .
H6B H 0.110211 0.308518 0.114369 0.063 Uiso 1 1 calc R U . . .
H6C H 0.181475 0.383645 0.174140 0.063 Uiso 1 1 calc R U . . .
C7 C 0.2062(3) 0.18916(17) 0.2459(2) 0.0350(6) Uani 1 1 d . . . . .
H7A H 0.280301 0.155420 0.275598 0.053 Uiso 1 1 calc R U . . .
H7B H 0.166678 0.164930 0.182564 0.053 Uiso 1 1 calc R U . . .
H7C H 0.139171 0.192669 0.292418 0.053 Uiso 1 1 calc R U . . .
C8 C 0.8235(2) 0.41570(13) 0.27302(16) 0.0179(4) Uani 1 1 d . . . . .
C9 C 0.7848(2) 0.41494(14) 0.16968(17) 0.0218(5) Uani 1 1 d . . . . .
H9 H 0.726430 0.373784 0.141201 0.026 Uiso 1 1 calc R U . . .
C10 C 0.8301(2) 0.47331(15) 0.10792(17) 0.0238(5) Uani 1 1 d . . . . .
H10 H 0.803641 0.472191 0.037519 0.029 Uiso 1 1 calc R U . . .
C11 C 0.9139(2) 0.53296(14) 0.15008(17) 0.0223(5) Uani 1 1 d . . . . .
C12 C 0.9533(2) 0.53601(15) 0.25252(18) 0.0241(5) Uani 1 1 d . . . . .
H12 H 1.010740 0.577767 0.280546 0.029 Uiso 1 1 calc R U . . .
C13 C 0.9076(2) 0.47722(14) 0.31350(17) 0.0212(5) Uani 1 1 d . . . . .
H13 H 0.933931 0.478880 0.383893 0.025 Uiso 1 1 calc R U . . .
C14 C 0.8525(2) 0.20512(13) 0.36157(17) 0.0182(4) Uani 1 1 d . . . . .
C15 C 0.9349(2) 0.17450(13) 0.44311(18) 0.0225(5) Uani 1 1 d . . . . .
H15 H 0.944708 0.203011 0.505088 0.027 Uiso 1 1 calc R U . . .
C16 C 1.0031(2) 0.10211(15) 0.43432(19) 0.0268(5) Uani 1 1 d . . . . .
H16 H 1.058272 0.080568 0.490360 0.032 Uiso 1 1 calc R U . . .
C17 C 0.9897(2) 0.06204(14) 0.3435(2) 0.0262(5) Uani 1 1 d . . . . .
C18 C 0.9057(2) 0.08963(15) 0.26235(19) 0.0266(5) Uani 1 1 d . . . . .
H18 H 0.895354 0.060380 0.200911 0.032 Uiso 1 1 calc R U . . .
C19 C 0.8365(2) 0.16111(15) 0.27219(18) 0.0225(5) Uani 1 1 d . . . . .
H19 H 0.777134 0.180400 0.217061 0.027 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 Sn C14 118.17(8) . . ?
C8 Sn Cl1 97.24(6) . . ?
C14 Sn Cl1 96.27(6) . . ?
C8 Sn S1 116.79(6) . . ?
C14 Sn S1 123.79(6) . . ?
Cl1 Sn S1 87.756(19) . . ?
C8 Sn S2 96.10(6) . . ?
C14 Sn S2 92.99(6) . . ?
Cl1 Sn S2 157.769(19) . . ?
S1 Sn S2 70.343(17) . . ?
C1 S1 Sn 89.51(8) . . ?
C1 S2 Sn 84.54(8) . . ?
C1 N1 C2 124.7(2) . . ?
C1 N1 C5 119.46(19) . . ?
C2 N1 C5 115.61(18) . . ?
N1 C1 S2 122.76(17) . . ?
N1 C1 S1 121.66(18) . . ?
S2 C1 S1 115.58(13) . . ?
N1 C2 C4 112.9(2) . . ?
N1 C2 C3 112.8(2) . . ?
C4 C2 C3 113.7(2) . . ?
N1 C2 H2 105.5 . . ?
C4 C2 H2 105.5 . . ?
C3 C2 H2 105.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C7 109.8(2) . . ?
N1 C5 C6 112.6(2) . . ?
C7 C5 C6 112.0(2) . . ?
N1 C5 H5 107.4 . . ?
C7 C5 H5 107.4 . . ?
C6 C5 H5 107.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.6(2) . . ?
C13 C8 Sn 121.33(16) . . ?
C9 C8 Sn 120.00(16) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 121.5(2) . . ?
C10 C11 Cl2 119.25(18) . . ?
C12 C11 Cl2 119.23(18) . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C15 C14 C19 118.9(2) . . ?
C15 C14 Sn 122.18(16) . . ?
C19 C14 Sn 118.74(16) . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 121.7(2) . . ?
C18 C17 Cl3 119.22(19) . . ?
C16 C17 Cl3 119.09(19) . . ?
C17 C18 C19 118.6(2) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C14 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn C8 2.139(2) . ?
Sn C14 2.141(2) . ?
Sn Cl1 2.4559(5) . ?
Sn S1 2.4589(5) . ?
Sn S2 2.6380(5) . ?
Cl2 C11 1.740(2) . ?
Cl3 C17 1.739(2) . ?
S1 C1 1.755(2) . ?
S2 C1 1.719(2) . ?
N1 C1 1.321(3) . ?
N1 C2 1.496(3) . ?
N1 C5 1.499(3) . ?
C2 C4 1.520(4) . ?
C2 C3 1.525(4) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C7 1.515(4) . ?
C5 C6 1.516(4) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.393(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 C19 1.394(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(4) . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 S2 175.30(18) . . . . ?
C5 N1 C1 S2 1.0(3) . . . . ?
C2 N1 C1 S1 -4.0(3) . . . . ?
C5 N1 C1 S1 -178.35(16) . . . . ?
Sn S2 C1 N1 179.1(2) . . . . ?
Sn S2 C1 S1 -1.48(11) . . . . ?
Sn S1 C1 N1 -179.03(19) . . . . ?
Sn S1 C1 S2 1.58(12) . . . . ?
C1 N1 C2 C4 68.2(3) . . . . ?
C5 N1 C2 C4 -117.3(2) . . . . ?
C1 N1 C2 C3 -62.5(3) . . . . ?
C5 N1 C2 C3 112.0(2) . . . . ?
C1 N1 C5 C7 104.1(2) . . . . ?
C2 N1 C5 C7 -70.7(3) . . . . ?
C1 N1 C5 C6 -130.4(2) . . . . ?
C2 N1 C5 C6 54.8(3) . . . . ?
C13 C8 C9 C10 0.9(3) . . . . ?
Sn C8 C9 C10 -176.97(17) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C9 C10 C11 Cl2 -179.88(18) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
Cl2 C11 C12 C13 -179.98(18) . . . . ?
C11 C12 C13 C8 0.1(3) . . . . ?
C9 C8 C13 C12 -0.8(3) . . . . ?
Sn C8 C13 C12 177.09(17) . . . . ?
C19 C14 C15 C16 1.8(3) . . . . ?
Sn C14 C15 C16 -174.00(18) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C15 C16 C17 C18 -3.1(4) . . . . ?
C15 C16 C17 Cl3 175.69(18) . . . . ?
C16 C17 C18 C19 2.1(4) . . . . ?
Cl3 C17 C18 C19 -176.72(19) . . . . ?
C17 C18 C19 C14 1.0(4) . . . . ?
C15 C14 C19 C18 -2.9(3) . . . . ?
Sn C14 C19 C18 173.09(18) . . . . ?
